Cheap flights from Orlando to Chicago from $37
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando to Chicago departing on 7/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Orlando to Chicago
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Frontier flights from Orlando to Chicago
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How to get the cheapest flight ticket from Orlando to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Orlando and Chicago?
What is the cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $133. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Orlando to Chicago during August average around $161.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $237. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $449.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando to Chicago during this time can be as low as $193. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $654.
What is the cheapest Orlando to Chicago flight route?
Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Orlando when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $223 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as $187 on momondo.
What cabin class options are available on Orlando to Chicago flights?
There are 4 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Orlando to Chicago?
Allegiant Air, Spirit Airlines, and Frontier are the most popular carriers operating from Orlando to Chicago
What airlines fly to Chicago?
Frontier, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Orlando according to our data. Frontier is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Orlando to Chicago on average per day?
As of June 2025, there are 57 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 2:00PM, with 50% of flights taking off in the afternoon.
How many flights depart from Orlando to Chicago on average per week?
As of June 2025, 405 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% of weekly flights taking off on this day.
When to book flights from Orlando to Chicago
Cheap Orlando to Chicago (ORL to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago
How far is Orlando to Chicago by plane?
Chicago is 985.3 mi away from Orlando. 2h 39m is a normal flight duration for this route.
When did momondo last update prices for flights from Orlando to Chicago?
Prices for flights from Orlando to Chicago refresh daily.
How many operators does momondo search for flights from Orlando to Chicago?
The number of operators available for flights from Orlando to Chicago is 7 as of June 2025.
How old do you have to be to fly from Orlando to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Orlando to Chicago?
Based on momondo bookings for flights between Orlando and Chicago, the leading plane model is Airbus A321neo, making up 20.77% of the total bookings. Other popular models include Airbus A320neo with 14.11%, Boeing 737 MAX 8 with 10.17%, and Boeing 737-800 with 9.96%.
What is the most popular airline from Orlando to Chicago?
momondo data reveals that the most frequently booked airline on the route from Orlando to Chicago is Frontier, representing 55% of all bookings. The subsequent popular airlines are American Airlines at 17%, Spirit Airlines at 14%, and United Airlines at 7%.
Best airlines flying from Orlando to Chicago
Compare and see reviews for airlines that fly from Orlando to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $66 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $72 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 7.3 725 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $158 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $181 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,950 reviews |
Southwest Flights From Orlando to Chicago
Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 70 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $181 round-trip, up to an average price of $338. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Orlando to Chicago
$157 is the best United Airlines flight deal from Orlando to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $329, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,790 user reviews) flies into Chicago from Orlando 33 times in an average week so prices can vary.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Orlando to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Orlando to Chicago with flexible booking policies on momondo?
Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Orlando to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Orlando.
I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.